Protocatechuic aldehyde

Protocatechuic aldehyde is a phenolic aldehyde, a compound released from cork stoppers into wine.[1]

Protocatechuic aldehyde
Chemical structure of protocatechuic aldehyde
Names
Preferred IUPAC name
3,4-Dihydroxybenzaldehyde
Other names
Protocatechualdehyde
Rancinamycin IV
3,4-Dihydroxybenzyl aldehyde
Identifiers
3D model (JSmol)
774381
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.889
EC Number
  • 205-377-7
123001
KEGG
UNII
  • InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H ☒N
    Key: IBGBGRVKPALMCQ-UHFFFAOYSA-N ☒N
  • InChI=1/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
    Key: IBGBGRVKPALMCQ-UHFFFAOYAN
  • C1=CC(=C(C=C1C=O)O)O
Properties
C7H6O3
Molar mass 138.12 g/mol
Related compounds
Related compounds
 2,4-Dihydroxybenzaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

This molecule can be used as a precursor in the vanillin synthesis by biotransformation by cell cultures of Capsicum frutescens, a type of Chili pepper.[2] It is also found in the mushroom Phellinus linteus.[3]

Pharmacological effects

Protocatechuic aldehyde regulates G protein-coupled estrogen receptor-1 (GPER-1) and exhibits protective effects in endothelial dysfunction and atherosclerosis.[4]

References
  1. Conde E, Cadahía E, García-Vallejo MC, Fernández de Simón B (August 1998). "Polyphenolic Composition of Quercus suber Cork from Different Spanish Provenances". Journal of Agricultural and Food Chemistry. 46 (8): 3166–71. doi:10.1021/jf970863k.
  2. Rao SR, Ravishankar GA (January 2000). "Biotransformation of protocatechuic aldehyde and caffeic acid to vanillin and capsaicin in freely suspended and immobilized cell cultures of Capsicum frutescens". Journal of Biotechnology. 76 (2–3): 137–46. doi:10.1016/s0168-1656(99)00177-7. PMID 10656328. S2CID 28017446.
  3. Lee YS, Kang YH, Jung JY, Lee S, Ohuchi K, Shin KH, et al. (October 2008). "Protein glycation inhibitors from the fruiting body of Phellinus linteus". Biological & Pharmaceutical Bulletin. 31 (10): 1968–72. doi:10.1248/bpb.31.1968. PMID 18827365.
  4. Kong BS, Cho YH, Lee EJ (2014). "G protein-coupled estrogen receptor-1 is involved in the protective effect of protocatechuic aldehyde against endothelial dysfunction". PLOS ONE. 9 (11): e113242. Bibcode:2014PLoSO...9k3242K. doi:10.1371/journal.pone.0113242. PMC 4239058. PMID 25411835.

See also
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